


Roadmap to Happiness

by doctor__idiot



Series: SPN Kink Bingo 2016 [4]
Category: Supernatural
Genre: Alternate Universe, Dean is Lorelai, First Kiss, Fluff, Gilmore Girls AU, Hurt/Comfort, I can't believe I actually wrote this, M/M, Sam is Luke, Sick!Dean, Supernatural Kink Bingo 2016
Language: English
Status: Completed
Published: 2016-10-09
Updated: 2016-10-09
Packaged: 2018-08-20 12:23:10
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,200
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8248801
Author URL: https://archiveofourown.org/users/doctor__idiot/pseuds/doctor__idiot
Summary: Gilmore Girls AUThe one where Sam is a reluctantly bemused diner owner and Dean is a long-suffering dad with a serious caffeine addiction.





	

**Author's Note:**

> I ... have no excuse for this. It got really long, too. I apologize for the lack of smut.
> 
> Written for the [SPN Kink Bingo](http://spnkinkbingo.tumblr.com) prompt "Friends to Lovers".
> 
> Disclaimer: Nothing's mine, except for the typos. Unbeta'd.

“You wouldn’t believe the day I’m having.”

Sam had the coffee pot at the ready the moment Dean walked into the diner, and now he was filling up the mug that was clutched between Dean’s hands as if he was hanging onto it for dear life. Which, to be fair, he probably was.

Dean impatiently snatched the cup away before Sam had finished pouring and some of the black liquid sloshed onto the counter. Dean didn’t seem to notice. 

Usually preferring a bit of cream and sugar, he only drank his coffee black on particularly stressful days. Sam could practically smell the overly dramatic tirade coming on from a mile away.

He sighed and wiped away the spillage with a practiced motion of his hand.

“So,” he prompted, trying to get it over with as quickly as possible. Ripping the band aid off. “How was your day?”

Dean shook his head. “Don’t get me started,” but he already was, “I gave Claire my phone yesterday because it was acting up and you know I’m helpless with that stuff…”

Didn’t Sam just.

“… but she must have messed with something because my alarm didn’t go off this morning. Means, I was late to work and today’s the wedding and the flower shipment was supposed to arrive at 8. Well, it did, but since I wasn’t there, they didn’t know what to do with it and they left the entire arrangement in the hall. Five thousand red tulips, Sam! … Why are you laughing?”

“I’m not,” Sam argued, pressing his lips together to prevent a snort, and kept wiping down the counter.

Dean huffed. “So, the staff, some of the guests, and yours truly tried to maneuver all of the flowers into the back yard before all the wedding guests arrive. We managed, no thanks to Garth, who just kept _sneezing_ , and in doing so knocked over some of the bouquets as well. And I’m wearing two different socks.”

Sam felt like he had been left behind at one of the stations Dean’s train of thought had passed in the last few minutes. “You what?”

Dean looked at him as if Sam had personally betrayed him. “I woke up _late_. Have you been listening to anything I just said?”

“I have, I just didn’t make that connection. I will pay better attention from now on.”

“You’re not taking me seriously.”

Chuckling, Sam grabbed the coffee pot and refilled Dean’s mug without having to be asked. “I’m not laughing at _you_ , if that’s any consolation. Not really anyway.”

“Whatever,” Dean sighed, rubbing his eyes. “I’ve got half an hour before I have to head back and check on the cake. God knows Charlie could already have burned down the entire building.”

Sam smiled. “Cheeseburger and fries?”

“God, yes, please. Don’t skimp on the bacon.”

Sam briefly turned his attention to a customer who ordered large fries to go. He shoveled a few handful of frozen French fries into the bubbling deep fryer before leaning back against the counter.

“When have you known me to ever skimp on anything?” He raised his eyebrows, nodding towards Dean’s half-empty coffee cup.

Dean snorted drily. “Every time you deem it appropriate to lecture me about my ‘unhealthy’ eating habits.”

He actually drew quotation marks into the air with his fingers and Sam shook his head in amusement, not seeing the point in replying.

“I would never,” he insisted, schooling his features into seriousness, “Not when you’re having such a brutal day.”

Dean didn’t appear fazed by the dig. He kept sipping his coffee. “You go right ahead and make fun of me,” he said, “It’ll all come back to bite you in the ass some day.”

Sam doubted that.

The little bell above the door chimed when it opened and in skidded another, substantially younger and blonder Campbell.

“Claire,” Sam called to her before she had even reached the counter, “Please talk some sense into your father.”

“Sure,” she said, sounding slightly out of breath as she collapsed onto a bar stool next to her dad. “In a minute, though. Get me some chili cheese fries first, I’m _starving_.”

“Ha!” Dean pointed a finger at Sam, who was confined to rolling his eyes and obeying the lady’s wish.

“Fine,” he said, more bemused than anything else, “If you so desperately want to give yourself a heart attack before you’re forty-five, you go right ahead.”

Dean made a non-committal sound and Claire blew a piece of hair out of her face. “Seriously,” she said, raising her eyebrows at Sam, “When are you gonna take down the sign outside?”

“Yeah,” Dean agreed, “When are you gonna hang one up that says ‘Sammy’s’? You could get one of those wooden ones on little chains that sway with the wind. Old-school.”

Claire perked up. “Can I design the font?”

Sam sighed ever so wearily. “What are you talking about?”

A simultaneous groan came from both Dean and Claire. “The sign,” they said, once again, in unison. 

“It says ‘Winchester & Sons’,” Sam said, stating the obvious. “That’s what this place is called. It used to be my dad’s and now it’s mine.”

“It’s a stupid name,” said Claire.

“It’s too long,” argued Dean. “It’s ‘Sammy’s’. That’s what everyone calls it.”

Sam didn’t bother engaging any further than responding with, “That only tells me that the majority of people in this town can’t read.”

By the time he had piled burgers and fries onto plates, Claire and Dean were busy making up more names for the diner and drawing preliminary sign designs on paper napkins.

Sam wordlessly placed the plates in front of them and went to serve other customers.

-=-

“Marco?” Claire called out from the hallway. Dean could hear her drop her keys into the bowl by the door.

“Polo,” he answered from the kitchen, pouring himself another cup of coffee. “What are you doing here so early?”

Claire rounded the corner and, with a thud, deposited the huge laundry basket she was carrying on the kitchen table.

She shrugged, tucking a piece of hair behind her ear. “I missed you.”

Dean hummed. “Or my washing machine.”

She grinned before heading straight for the coffee maker, pouring what was left of the coffee into a cup for herself.

“How’s school?”

She shrugged again. “Fine. Nothing newsworthy happened, if that’s what you’re getting at.”

Dean crossed his ankles under the table, pursing his lips. “How’s …”

“Kevin?” Claire lifted an eyebrow accusingly. “He’s good.”

“You’re still together then.”

“We are.” Her tone was no-nonsense and there was a crease to the side of her mouth. Dean decided not to open that particular can of worms this morning.

“Scrawny kid,” Dean said, just to be annoying, and took another sip of his coffee. It scalded his tongue but it was too delicious to slow down.

Claire rolled her eyes, plopping down on another chair with her mug. “He’s not. Just because you prefer your men extra-beefy, you don’t need to rag me about my choices.”

Dean snorted. “Fair enough.”

“Speaking of which…”

Dean did not like the sound of ‘Speaking of which…’ in combination with beefy men. Not when his daughter had that particularly mischievous glint in her eyes like she did now. In his experience, that glint never boded well for him.

“What?”

Claire sipped her coffee. “Are you seeing anyone?”

Dean set his jaw. “You would know it if I was.”

She sighed. “Dad, you seriously need to get out more.”

Dean bristled. “I get out plenty.”

“Working, going to town meetings, and babysitting for Jody is not ‘getting out’.”

Dean would tell his daughter to stay the hell out of his business if she wasn’t so right. 

He went on a couple of dates with a guy he had met at Claire’s first-semester welcome week but after the first evening, if was fairly obvious to both of them that it wasn’t going anywhere. Dean didn’t say anything until after the second date because the guy was really hot and Dean was kind of lonely, sue him.

But all the hotness and loneliness in the world couldn’t justify incompatibility. Plus, Dean was really too old for one-night-stands and short flings that didn’t lead anywhere. Even if he could barely admit it, he truly longed for someone he could actually imagine spending the rest of his life with.

Guys like that didn’t exactly grow like weed. More like one of those super-rare plants that probably only grew in New Zealand or something.

Dean really didn’t want to have to go to New Zealand to find someone worth his time.

He pointed a finger at Claire. “Don’t forget the dog-walking I do for Missouri.”

“I should probably give you credit for the trips to the grocery store as well.”

Dean nodded. “You sure should.”

“What about Sam?”

Dean nearly dropped his mug. As it was, he spluttered, the coffee sloshed precariously, and he set it down onto the table with a clank before it could spill everywhere.

“What?”

Claire looked at him with an innocent expression. “You must have thought about it, at least. I mean, newsflash: He’s kind of perfect for you.”

“I…” Dean was at a loss for words. Partially, because they had never actually had a serious conversation about him dating … anyone, for that matter. He had always tried to keep Claire out of that part of his life because he didn’t want her to get attached to anyone who wasn’t in it for the long haul. 

For the most part, however, he didn’t know what to say in his defense because he had none. He had thought about it. About him. Sam. Him and Sam. 

_Him and Sam_. Jesus H. Christ.

If he was perfectly honest with himself, he had been too much of a pussy so far to show Sam that he was interested. Hell, he wasn’t even all that sure he was interested.

His and Sam’s friendship was pretty much the most amazing thing – next to his daughter but that goes without saying – he had in his life and he wasn’t sure he was ready to risk that just because Sam was … beefy.

He shook his head, partly as a response to Claire’s question, but mostly to clear it a little. “I don’t…”

Claire pursed her lips the same way he had earlier and he could swear her drawn-up eyebrow was _knowing_ , as much as eyebrows could be knowing.

__He emptied his mug in one big gulp and pushed up from his chair. “I better get started on that laundry.”_ _

__He snatched the basket from the table top and set it on his hip when he climbed the stairs. He could hear Claire muttering something on his way up and it sounded suspiciously like “Coward.”._ _

__He winced._ _

__-=-_ _

__Dean hadn’t thought it was possible to ever, in his life, feel worse than when he had been chained to his bed for two weeks by pneumonia a couple of years ago._ _

__As it turned out, it was very well possible._ _

__“You’re such a wuss,” his daughter helpfully provided as she squeezed her feet into her boots and grabbed her book bag._ _

__Dean didn’t stoop to answer but that was mainly because his head was throbbing so hard that even opening his mouth to say something would have sent a spike of pain through the right side of his brain._ _

__He closed his eyes and tried not to throw up._ _

__He had to admit, taking several steps at a time to mount the stairs, only to slip and crack his head open against the top stair hadn’t been one of his more brilliant achievements. He had been late, goddammit. Again._ _

__Now, his head was pulsing angrily and he was nauseous and dead-tired because the monsters at the hospital who called themselves doctors had kept him up all night. He still winced when he thought back to the pain of that small flashlight being shown into his eyes._ _

__“All right,” Claire said, “I gotta go. I told Sam to check on you in a bit and make sure you didn’t roll off the couch and hit the other side of your head as well.”_ _

__“I’m not that clumsy.” He grimaced when he remembered why speaking was a bad idea._ _

__Claire snorted derisively and apparently didn’t deem it necessary to respond to that._ _

__Despite his expectations, Dean fell asleep pretty quickly after Claire had left for school. His head hurt but he was tired enough to slip into a dozing state after awhile and lying down, he wasn’t as dizzy as he had been before._ _

__He was startled by the sound of the front door opening and closing and he sat up too quickly. The dizziness came rushing back him and for a split-second he was convinced he was going to puke._ _

__He gasped, supporting himself on his thighs and breathed through the onslaught by his abused brain. The pain wasn’t actually as bad as it had been before he went to sleep, but it was still bad enough to make him close his eyes because the little amount of light that snuck though the drawn curtains was enough to make him see stars._ _

__“Hey,” came a soft voice from a few feet away and Dean slowly turned his head into that direction._ _

__He found that when he moved very very slowly, the pain was actually manageable._ _

__Sam smiled at him. “How you feeling?”_ _

__Dean returned the smile weakly. “Like I’m eight years old and I want my mom to hold my hand.”_ _

__Sam laughed and even though the sound was already almost too loud for Dean, it was sort of nice regardless. “I know that feeling. Well, I’m not your mom but I can still hold your hand if you want,” he grinned, “Do you want anything to eat or drink while I’m here?”_ _

__Dean shook his head slowly but not slowly enough because the ache flared up again. He instinctively reached for the painful spot. To prevent him from scratching or touching the wound, they had taped a gauze pad over the stitching and Dean carefully fingered the edge of it._ _

__“Get your hands off that,” Sam said, gently enough not to make Dean’s head throb again but firmly enough that Dean immediately pulled his hand away._ _

__Sam vanished into the kitchen and came out with a glass of water, although Dean had negated his inquiry. It wasn’t a new thing for Sam to completely disregard Dean’s food and drink choices if he thought they weren’t suitable._ _

__Dean remembered a time where Sam had actually _bodily_ prevented him from drinking the red wine instead of the white because ‘it just doesn’t go with the dish’._ _

__Dean took the glass of water and started sipping slowly because he couldn’t be sure Sam wouldn’t physically force it down his throat._ _

__“I think you’d feel better if you could lie down in bed. Think you can make it up the stairs?” Sam took the glass from him when it was empty. Dean had to admit the water made him feel, if only marginally, better._ _

__“I’ve got a concussion, Sam, I didn’t break my legs.”_ _

__Sam snorted. “Be glad you didn’t. Wanna go upstairs then?”_ _

__The couch in the living room was really rather made for lounging on to watch TV, not to host a 6-foot-something invalid, who was already feeling a twinge in his back from his nap earlier._ _

__Dean groaned pitifully as he stood up. “Yeah, bed sounds awesome.”_ _

__He tried not to think about all the different connotations of the thought of Sam and him climbing the stairs to Dean’s bedroom together had. Dean decided to blame it on the concussion that his brain was cooking up scenarios that were significantly less PG than what was actually happening._ _

__When they reached the top of the stairs, Dean was so intent on not focusing on Sam’s presence behind him and how much he wanted Sam to not only follow him into the bedroom but also into bed, that Dean missed a step. Quite literally, and, in a ridiculous version of déjà-vu, he already saw himself crashing into the wall head-first all over again._ _

__His hands shot out on instinct to brace himself, but this time, as soon as he tripped, his fall was halted by Sam’s arm around his waist._ _

__Dean was jerked back against Sam’s chest, back onto his feet. Pain exploded behind his temples and he whimpered. Bile rose in his throat and he pressed his mouth against his own biceps in order not to throw up, even if there wasn’t anything in his stomach that could have made its way onto the plush carpet._ _

__He was dimly aware of Sam swearing under his breath and his own trembling – whether from the pain or the shock, he wasn’t sure – but he was too focused on breathing against the dizziness and nausea to take note of much else._ _

__“You okay?” Sam asked softly, his voice right next to Dean’s ear. He was practically whispering as not to aggravate Dean’s head any further and Dean genuinely appreciated the effort._ _

__He didn’t dare nod his head, so he just briefly squeezed Sam’s arm that was still tightly wrapped around his middle in lieu of answer._ _

__“How you managed to survive all these years without sustaining any major injuries is a mystery to me.”_ _

__Sam’s sarcasm on the other hand was not appreciated. Not when Dean couldn’t turn around and glare at him without getting attacked by more dizziness._ _

__Sam slowly, almost reluctantly, released him but kept his hand at Dean’s hip as if he was worried Dean would take another nose-dive any second. Dean shivered at the gentle touch._ _

__Sam steered him towards the bedroom and waited by the side of the bed until Dean was safely under the covers and not in any more danger of stumbling, falling, banging against furniture, or even just stubbing his toe._ _

__“Do you want something to eat?”_ _

__Dean carefully shook his head. “I’d just puke it up. I’m fine. Just tired.”_ _

__Sam smiled softly. “Did they give you painkillers at the hospital? To help you sleep?”_ _

__“Yeah.” Dean closed his eyes, the corner of his mouth curling up. “But they make me feel funny. Don’t want them. It doesn’t even hurt that much if I don’t move.”_ _

__He could already feel himself drifting off, hearing Sam’s voice as if through cotton. “Okay, I’ll be downstairs if you need anything.”_ _

__Dean wanted to tell Sam that he didn’t have to stay but he was too exhausted to manage it. He would probably be wasting his breath, too._ _

__Then Sam said something that pulled Dean back from the edge of delicious slumber. His eyes snapped open. “What?”_ _

__Sam’s cheek were coloring. “I wanted to know if you wanna get out of those clothes. What I _meant_ , you pervert, was that you might be more comfortable not wearing your jeans.”_ _

__Dean stared at him. Sam’s cheeks and the point of his nose was tinged red, showing his embarrassment. Dean would laugh if it wasn’t so adorable._ _

And he _was_ kind of uncomfortable, so he nodded and unbuttoned his pants, shimmying them down off his hips.

__“Would you mind?” he asked Sam, who seemed to be rooted to the spot, looking down at Dean, before he inhaled sharply and moved to the end of the bed, tugging on both of Dean’s pant-legs. He folded the article of clothing neatly and draped it over a chair._ _

__To Dean it seemed as if Sam was hesitating, hovering, wanting to say something else, do something else, but he could be imagining things. He had a concussion after all._ _

__And it was precisely that concussion that made him grab for Sam again when the man was already on his way out the door. Dean didn’t even realize he had reached out until his saw his own fingers wrapped around Sam’s wrist._ _

__Sam froze next to the bed. “Dean?”_ _

__Dean licked his dry lips. He should have brought some water upstairs with him but he couldn’t be bothered to get up now. He’d make Sam get him some. Later._ _

__“Can you…“_ _

__Dean stopped himself, not wanting to be too needy, too obvious, too … desperate. He didn’t want to bet all his money on one hand if it wasn’t a straight flush, or at the very least a full house._ _

__But the way Sam was looking at him right now made him want to go all in. He could always blame it on the concussion._ _

__“Can you stay here?”_ _

__Sam’s eyes widened, smart mouth lost for words, but he didn’t extricate his wrist from Dean’s grip. Dean felt himself tremble again and this time for a completely different reason._ _

__Sam didn’t say anything and Dean was starting to get worried that it had been the wrong move after all, but then Sam’s shoulders slumped, he exhaled, and sat down on the edge of the mattress._ _

__Dean released his wrist. Shoved his hands underneath his pillow so he wouldn’t be tempted to touch._ _

__Sam lay down facing him. Dean was all too aware of their proximity, of Sam’s face this close to his, heat radiating from Sam’s body, seeping into Dean’s limbs. He could almost feel Sam’s even breaths ghosting over his skin._ _

__Without thinking he reached for Sam’s belt buckle._ _

__Sam’s hand shot forward, gripping Dean’s wrist in the same way Dean did earlier. “What are you doing?”_ _

__Dean cleared his throat. “I thought you might be more comfortable without your jeans, too.”_ _

__He wasn’t even sure himself that was all there was to it. Clearly, Sam didn’t think that was the whole truth, either, if his wary eyes were anything to go by._ _

__Truth was, Dean wasn’t sure of much of anything these days. All he knew was that, right now, he was tired and hurting and Sam was right there, and he couldn’t deny that he wanted … something. Wanted Sam._ _

__Not necessarily in the “I wanna fuck your brains out” kind of sense – phantom pain was flaring up in his head just thinking about it – but in the “I want you near me at all times” kind of sense, and that was just downright scary. Plus, he didn’t even know what Sam wanted._ _

__Although Sam wasn’t exactly jumping up in shock, protesting loudly, or pushing him away, so he might not be opposed to either idea. In fact, save for the hold he had on Dean’s wrist – which loosened more by the second –, Sam hadn’t moved at all. Their knees were almost touching._ _

__Sam finally let go of Dean to rid himself of his clothes until he was lying next to Dean in only his T-shirt and his boxer shorts. His eyes were intently focused on Dean’s face and Dean swallowed thickly._ _

“I don’t…” _know what to do_. He cut himself off.

__“You should get some sleep,” Sam said eventually and Dean nearly sighed in relief. He nodded slowly, headache all but a dull throb now._ _

__As soon as he had closed his eyes, he noticed how leaden his exhaustion actually was. He probably wouldn’t be able to raise his lids again if he tried._ _

__He blindly reached for Sam’s chest, flattening his palm right over the space where he could feel the strongest heartbeat and he swore Sam’s heart stumbled under his fingertips._ _

__Sam’s fingers were back around his wrist, not pushing or pulling, just holding._ _

__Dean smiled with his eyes closed, and then nearly jumped out of his skin when he felt Sam’s lips press against his own._ _

__He heard himself make a surprised noise, eyelids fluttering, squinting to check that this was actually happening, and then he quickly wound an arm around Sam’s shoulders, not giving him a chance to pull back again._ _

__Sam chuckled against Dean’s mouth and wrapped an arm of his own around Dean’s middle, gently tugging him closer._ _

__Dean distantly felt his hand shaking where it was pressed against Sam’s chest. He curled his fingers in the fabric of Sam’s shirt to stop the tremble and kissed Sam harder, giving a little grunt of pain when their teeth collided somewhat uncomfortably and the impact jarred Dean’s brain._ _

__He didn’t pull back, though, opening his mouth against Sam’s and for a moment it was as if they were simply _breathing_ each other in._ _

__Then Sam lightly nipped Dean’s bottom lip and Dean moaned._ _

__“It’s not nice to take advantage of a man with a concussion,” he panted against Sam’s mouth, already breathless from less than two minutes of kissing._ _

__“Easy prey,” Sam said, grinning, and Dean shivered._ _

__He closed his eyes when the tip of Sam’s index finger brushed gently along his cheek bone._ _

__Sam kissed him again, briefly, chastely, whispered, “Sleep.”_ _

__Dean made a disapproving noise in the back of his throat but he had to admit that he was about two seconds away from slipping away, pain and nausea finally taking their toll._ _

__“Stay,” he managed to say and shortly after, he felt Sam’s hand in his hair._ _

__“Not going anywhere. I’ll be here.”_ _

__Dean muttered, “Took you long enough,” and he heard Sam chuckle before he finally fell asleep._ _


End file.
